Ethanol → Ethyl 2-isopropyl-5-oxo-1-imidazolidineacetate

HRID 1608013Notes

Reaction equation

HRID 1608013 reaction equation
S(Cl)(Cl)=O.[CH3:5][CH:6]([CH:8]1[NH:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][C:15]([O-:17])=[O:16])[CH3:7].[Na+].[CH2:19](O)[CH3:20]>>[CH3:7][CH:6]([CH:8]1[NH:12][CH2:11][C:10](=[O:13])[N:9]1[CH2:14][C:15]([O:17][CH2:19][CH3:20])=[O:16])[CH3:5]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 23672396Sodium 2-(1-methylethyl)-5-oxo-1-imidazolidineacetate

Product 1

HCID 14618022Ethyl 2-isopropyl-5-oxo-1-imidazolidineacetateYield 42%

Conditions

Temperature
0 °C

Procedure

To 50 ml of anhydrous ethanol stirred at 0°-5° C., 2 ml thionyl chloride were added. At the same temperature 2.1 g (0.01 mol) of sodium 2-(1-methylethyl)-5-oxo-1-imidazolidineacetate were added. The obtained suspension was stirred at 0° C. for 1 hour and at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the residue taken up with ethyl acetate. The solid residue was filtered off and the solvent evaporated. The residue was dissolved in a saturated solution of sodium hydrogen carbonate and extracted with 3×50 ml of dichloromethane. The organic layers were evaporated to give ethyl 2-(1-methylethyl)-5-oxo-1-imidazolidineacetate (0.9 g) as a pale-yellow oil (42%) (Rf 0.6, ethyl acetate/dichloromethane 6:4; silica gel plates). Hydrochloride salt, m.p. 148°-149° C. (methanol/ethyl acetate).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. filtrationThe solid residue was filtered off
  3. customthe solvent evaporated
  4. dissolutionThe residue was dissolved in a saturated solution of sodium hydrogen carbonate
  5. extractionextracted with 3×50 ml of dichloromethane
  6. customThe organic layers were evaporated

Sources & evidence

ORD record
ord-682bade1079742c1b0020513d87e757d
Source dataset
uspto-grants-1989_09
Patent number
US04868313

Reaction notes

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